Water → HCID 70456511, compound

HRID 280602Notes

Reaction equation

HRID 280602 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH3:10])=[C:8]([CH2:11][C:12]3[NH:13][CH:14]=[CH:15][N:16]=3)[S:7][C:6]=2[CH:17]=1.O.[CH3:19][N:20](C)C=O>>[NH:16]1[CH:15]=[CH:14][N:13]=[C:12]1[CH2:11][C:8]1[S:7][C:6]2[CH:17]=[C:2]([C:19]#[N:20])[CH:3]=[CH:4][C:5]=2[C:9]=1[CH3:10]

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 70456989HCID 70456989, compound

Product 1

HCID 70456511HCID 70456511, compound

Procedure

A mixture of 6-bromo-2-(1-imidazolylmethyl)-3-methylbenzo[b]thiophene (1.01 g) and cuprous cyanide (1.80 g) in N,N-dimethylformamide (20 ml) was heated under reflux for 22 hours and then cooled and poured into water. The solid was filtered off, washed with water and then suspended in a mixture of concentrated aqueous ammonia solution (100 ml) and ethyl acetate (150 ml) and the mixture was stirred until no solid remained. The organic layer was separated, washed with water, dried (Na2SO4) and evaporated. The residue was crystallised from ethyl acetate/petrol (b.p. 60°-80°) to give 2-(1-imidazolylmethyl)-3-methylbenzo[b]thiophene-6-carbonitrile (0.58 g), m.p. 154°-155°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 22 hours
  3. temperaturecooled
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. additionsuspended in a mixture of concentrated aqueous ammonia solution (100 ml) and ethyl acetate (150 ml)
  7. customThe organic layer was separated
  8. washwashed with water
  9. dry with materialdried (Na2SO4)
  10. customevaporated
  11. customThe residue was crystallised from ethyl acetate/petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-336cd269ddec4617ba7635a65ddbd125
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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